Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Jamie Benson, Marketing Manager, Public Speaker & Performer, located in New York, NY, USA.

What's your business, and who are your customers?

I'm a freelance PR gun for hire, as well as a comedic writer and performance artist. When not swooping into arts and culture-making institutions to turn out ticket sales or pull in fundraising dollars, I'm attempting to make irreverent people laugh online and on stage.

Tell us about yourself

As a young dance school dropout with no pedigree, money, or industry connections, I was desperate to be seen as a creative person that exists. To adapt, I channeled my creativity into promoting my work as a comedic choreographer, cornering a small market of creatives who essentially make comedic sketches as dances.

Now, I help other creatives, and arts-based non-profits make waves for their work. This need to make the invisible visible motivates me to this day, whether for my clients or for myself.

What's your biggest accomplishment as a business owner?

As a self-employed marketing professional, some of the things I'm most proud of include securing more than $700,00 dollars for a music school that serves at-risk children, acquiring a New York Times feature for a dance company that champions disabled artists, and leading thousands of entrepreneurs in hilarious, action-oriented self-promotional workshops.

Personally, as an artist, I'm proud of getting my film work accepted into the New York Independent Film Festival, being awarded a creation residency from the Joyce Theater, being featured in the Phaidon Press Book "Wild Art," and receiving funding from the Brooklyn Arts Council.

What's one of the hardest things that comes with being a business owner?

The time commitment and sheer force of will be required in the beginning stages of launching almost anything of value is often even more work than you may think it is. Trial, error, and bouncing back from heartbreak can create quite the roller coaster experience.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Get comfortable with sharing what you learn as you go along. Speaking engagements and educational videos have created so much word of mouth I have to turn down work requests.
  2. Address objections people may have to your proposed services, and show off the ones that compliment them. Everyone's a critic about everything now, and trust is the most important thing to cultivate.
  3. This may sound odd, but you don't always need to be driven purely by passion and inspiration or even always believe in yourself. For me, it's been about consistently making room every day to sit with your ambitions and problem-solve whatever comes up. You'll gain motivation and momentum when you solve what seems impossible at first glance.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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